The following is a brief summary of some of thoughts said over by R' Frand on the parsha this evening. I have attempted to reproduce these vorts to the best of my ability. Any perceived inconsistency is the result of my efforts to transcribe the shiur and should not be attributed to R' Frand.
R' Frand observed that the parsha begins with the Mitzva of bringing Bikkurim - the first fruits - to the Beis HaMikdash. The Gemara discusses the parade of these fruits was they were brought up from the countryside and the encouragement to those who brought them. Once the farmer has arrived at the Beis HaMikdash he would recite the Mikra Bikkurim which is found in Devarim 26:5-10.
R' Frand quoted the Mishna in Bikkurim 3:7 which states that originally, those people who were able to read the Mikra Bikkurim would do so and those who could not were assisted by the Kohain. However, people who did not know how to read began to refrain to bring their fruits and it was enacted that everyone would be assisted by the Kohain.
However the next Mishna in Bikkurim seems to contrast with this concept. In Bikkurim 3:8, the Mishna explains that the wealthy people brought their fruits in gold and silver baskets, while the indigent would bring theirs in baskets made from woven palm branches. The Gemara adds that the wealthy people would have their baskets returned to them while the palm baskets were retained by the Kohain.
R' Isaac Bernstein asked the now obvious question - why did they not enact that everyone use the same basket so that there would be no embarrassment? He answers that not being literate is something to be embarrassed about, as everyone should be able to read and the learn the Torah. However, not being as wealthy as someone else is not a reason to be embarrassed and no enactment was required.
R' Frand said a second vort related to the Tochacha. Within these curses, the Torah states in Devarim 28:47 that they come about תַּ֗חַת אֲשֶׁ֤ר לֹא־עָבַ֙דְתָּ֙ אֶת־יְהֹוָ֣ה אֱלֹהֶ֔יךָ בְּשִׂמְחָ֖ה וּבְט֣וּב לֵבָ֑ב מֵרֹ֖ב כֹּֽל. This is commonly translated as the curses come because a person did not serve Hashem with happiness and a full heart.
But why should someone receive curses simply because he was not happy when he was performing Mitzvos. After all, he did go to Shacharis, or shook a Lulav, or separated Tithes. R' Frand quoted the Meshech Chachma who explains that you need to put a semi colon in the pasuk and read it as תַּ֗חַת אֲשֶׁ֤ר לֹא־עָבַ֙דְתָּ֙ אֶת־יְהֹוָ֣ה אֱלֹהֶ֔יךָ; בְּשִׂמְחָ֖ה וּבְט֣וּב לֵבָ֑ב מֵרֹ֖ב כֹּֽל - because you did not serve Hashem your G-d, as you were more interested in accumulating wealth and that's what made you happy. R' Frand said that its natural that a person is happy about things that he does. But if a person has no happiness in doing Mitzvos, he will find happiness in physical things. Thus the curses come because a person only had pleasure when he was accumulating wealth and as a result, he did not do Mitzvos.
R' Frand also said a vort about Rosh Hashanah which had some similarities to the second parsha vort. He observed that we blow the Shofar on Rosh Hashanah as the Torah calls it a Yom Teruah, but the laws of how the Shofar is blown are derived from Yoveil.
R' Frand quoted the Rambam in Hilchos Teshuva which writes that while the Mitzva of Shofar is learned from the Pesukim, it is hinted to based on a different pasuk in Nach which teaches that the Shofar is intended to wake us up from slumber and to do Teshuva. This is because people forget what is Emes and they spend their lives in nothingness.
R' Frand observed that when we hear Shofar we are not sleeping, but a person can be sleeping while they are wide awake. This is because we are so involved in what occupies our lives, we are spiritually sleeping and this is the alarm clock of Shofar.
R' Frand then quoted the Gemara in Rosh Hashana which discusses the laws of Shofar and its connection with Yom Kippur of Yoveil. The Shofar is blown on Yom Kippur of Yoveil when the Jewish slaves are freed and the ancestral lands are returned. R' Frand then quoted R' Emanuel Bernstein who asked - if Shofar is Teshuva, why are the laws learned from the financial rules of Yoveil? He answers that Yoveil is also a wake up call. A person can live on property 30-40 years and think this is mine. He sees the Eved Ivri who has been part of the household for 30 years and think - he belongs to me. Yoveil comes and tells the owner - you think the Eved or the land is yours? Its mine - you need to wake up and realize that they are Mine as the Torah states in Vayikra 25:23 - וְהָאָ֗רֶץ לֹ֤א תִמָּכֵר֙ לִצְמִתֻ֔ת כִּי־לִ֖י הָאָ֑רֶץ and 25:55 - כִּֽי־לִ֤י בְנֵֽי־יִשְׂרָאֵל֙ עֲבָדִ֔ים עֲבָדַ֣י הֵ֔ם אֲשֶׁר־הוֹצֵ֥אתִי אוֹתָ֖ם מֵאֶ֣רֶץ מִצְרָ֑יִם. This is the connection between the Shofar of Rosh Hashanah and Yoveil - you need to wake up from your slumber, even if you are wide awake.